Beta-benzoylacrylic acid → HCID 13476426, compound

HRID 1981868Notes

Reaction equation

HRID 1981868 reaction equation
[C:1]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([OH:17])(=[S:16])[CH3:15]>C(OCC)C>[C:14]([S:16][CH:10]([CH2:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]([OH:13])=[O:12])(=[O:17])[CH3:15]

Participants

4

Reactant 2

HCID 94714Beta-benzoylacrylic acidHCID 178418634HCID 178418634, compound

Product 1

HCID 13476426HCID 13476426, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.76 g of 3-benzoylacrylic acid in 30 ml of diethyl ether was added 0.8 ml of thioacetic acid, and the resulting mixture was stirred at room temperature for 5 hours. The diethyl ether was removed from the reaction mixture by evaporation under reduced pressure, and the residue was purified by silica gel column chromatography using a mixture of hexane and dichloromethane as an eluent and recrystallized from a mixture of hexane and diethyl ether to give 2.09 g of 2-acetylthio-3-benzoylpropionic acid.

Workup

  1. customThe diethyl ether was removed from the reaction mixture by evaporation under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. additiona mixture of hexane and dichloromethane as an eluent
  4. customrecrystallized from a mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-ef54c5abd7eb40c083658cdcd292418e
Source dataset
uspto-grants-1986_06
Patent number
US04594197

Reaction notes

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